Diisopropylethylamine → HCID 178426595, compound

HRID 1480372Notes

Reaction equation

HRID 1480372 reaction equation
[OH:1][C:2]1[CH:6]=[C:5]([CH2:7][CH2:8][C:9]([OH:11])=O)[O:4][N:3]=1.[NH2:12][CH2:13][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][CH2:23][C:24]2[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[CH:25]=2)=[O:21])[CH:16]([CH3:32])[CH2:15]1.CCN(C(C)C)C(C)C.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>CN(C=O)C>[OH:1][C:2]1[CH:6]=[C:5]([CH2:7][CH2:8][C:9]([NH:12][CH2:13][CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][CH2:23][C:24]3[CH:25]=[C:26]([Cl:31])[CH:27]=[C:28]([Cl:30])[CH:29]=3)=[O:21])[CH:16]([CH3:32])[CH2:15]2)=[O:11])[O:4][N:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 867226293,5-Dichlorobenzyl 4-(aminomethyl)-2-methylpiperidine-1-carboxylateHCID 1785253353-(3-Hydroxy-5-isoxazolyl)propanoic acid

Product 1

HCID 178426595HCID 178426595, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture comprising of 3-(3-hydroxyisoxazol-5-yl)propanoic acid (40.2 mg, 0.256 mmol), 3,5-dichlorobenzyl 4-(aminomethyl)-2-methylpiperidine-1-carboxylate (step 4) (84.7 mg, 0.128 mmol), Huenig's base (89 μl, 0.511 mmol) and T3P® (50% solution in DMF)(149 μl, 0.256 mmol) in DMF (426 μl) was left stirring at room temperature 18 hours. The resulting mixture was concentrated under pressure and diluted with water. The aqueous solution was extracted with EtOAc and the combined organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure. Further purification was carried out using preparative LC-MS. The resulting product fractions were concentrated under reduced pressure to give an aqueous solution and then extracted with EtOAc. The organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure to afford the title compound.

Workup

  1. concentrationThe resulting mixture was concentrated under pressure
  2. additiondiluted with water
  3. extractionThe aqueous solution was extracted with EtOAc
  4. dry with materialthe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customFurther purification
  8. concentrationThe resulting product fractions were concentrated under reduced pressure
  9. customto give an aqueous solution
  10. extractionextracted with EtOAc
  11. dry with materialThe organic extracts were dried over MgSO4
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d4c85acbdb3b4736aa2e764769d71a25
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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